Day & Evening Sails in Chicago, IL

Purchase the perfect gift card with a value of your choosing!

Enjoy unlimited Skyline Sails all season long with a Skyline Sails Membership! Bring friends and family along and enjoy exclusive discounts on their tickets.

Sail into Independence Day aboard Chicago’s Official Tall Ship Windy! Enjoy patriotic music, stunning skyline views, and a festive evening on the water.

Experience the thrill of Chicago’s Air & Water Show from the deck of Lakeshore Sail Charters! Enjoy unbeatable views as jets soar overhead and boats glide across the water.

Set sail for a magical evening and watch Navy Pier’s fireworks light up the sky! Enjoy stunning skyline views, a relaxing sail, and a drink from our onboard bar.